Triethylamine → Methyl L-prolinate

HRID 1625710Notes

Reaction equation

HRID 1625710 reaction equation
C(N(CC)CC)C.[NH:8]1[CH2:16][CH2:15][CH2:14][C@H:9]1[C:10]([O:12][CH3:13])=[O:11].Cl>CCOCC>[NH:8]1[CH2:16][CH2:15][CH2:14][C@H:9]1[C:10]([O:12][CH3:13])=[O:11]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 2733200methyl L-prolinate hydrochloride

Product 1

HCID 853477Methyl L-prolinateYield 70.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Triethylamine (8.4 mL) was added to H-Pro-OMe HCl (7.512 g) in ether (27 mL) and the reaction was stirred for 2 hours. The reaction mixture was filtered, and Et2O was removed by evaporation. The residue was purified by vacuum distillation, affording 4.119 g of H-Pro-OMe as colorless oil. t-BuOCl (3.59 mL) was added dropwise to an Et2O (100 mL) solution of H-Pro-OMe (4.089 g) and the reaction was stirred at −50° C. for 1 hour. The reaction mixture was warmed to room temperature and triethylamine (4.64 mL) was added to the reaction mixture, followed by stirring for 3 days. The reaction mixture was filtered, and concentrated under reduced pressure. The residue was purified by vacuum distillation to obtain Methyl pyrroline-2-carboxylate (3647-154) as a colorless oil. ESI-MS calculated for C6H9NO2 [MH]+: 128.1; observed: 128.2. 1H NMR (400 MHz, CDCl3): 4.09 (tt, J=7.6 Hz, 2.5 Hz, 2H), 3.85 (s, 3H), 2.81 (tt, J=8.2 Hz, 2.8 Hz, 2H), 1.97 (quintet, J=8.0 Hz, 2H). 13C NMR (100 MHz, CDCl3): 168.2, 163.1, 62.5, 52.5, 35.2, 22.1. ESI-MS calculated for C5H7NO2 [MH]+: 114.1; observed: 114.2. 1H NMR (400 MHz, D2O): 3.84 (tt, J=7.4 Hz, 2.5 Hz, 2H), 2.73 (tt, J=8.2 Hz, 2.6 Hz, 2H), 1.92 (quintet, J=7.8 Hz, 2H). 13C NMR (100 MHz, D2O): 175.5, 171.8, 60.1, 35.6, 21.8ESI-MS calculated for C5H7NO2 [MH]+: 114.1; observed: 114.2. 1H NMR (400 MHz, D2O): 3.84 (tt, J=7.4 Hz, 2.5 Hz, 2H), 2.73 (tt, J=8.2 Hz, 2.6 Hz, 2H), 1.92 (quintet, J=7.8 Hz, 2H). 13C NMR (100 MHz, D2O): 175.5, 171.8, 60.1, 35.6, 21.8.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customEt2O was removed by evaporation
  3. distillationThe residue was purified by vacuum distillation

Sources & evidence

ORD record
ord-094c78103b044226becf60bcc93c05dd
Source dataset
uspto-grants-2014_07
Patent number
US08785151B2

Reaction notes

Loading…